"Silver Wings" (1969)
Look around the room when Haggard sings this live, and the same scene unfolds: Someone is inevitably wiping away tears. From 1969's A Portrait of Merle Haggard, "Silver Wings" wasn't a Number One hit but has endured as one of his greatest heartbreakers, on par with Mickey Newbury at his most mournful. Romanticizing an airplane's "silver wings" that take away his lover, Haggard sang so intimately that you wondered if you were eavesdropping. Even the arrangement — with its slack guitar strums, soft brushes on the drums and a majestic wash of strings — felt like a sucker punch to the gut. Pass the Kleenex. J.R.